8-Hydrazino­quinoline di­hydro­chloride hydrate

The structure of the title compound, C₉H₁₁N₃·2Cl·H₂O, comprises a planar cation containing two quaternary N atoms, packed in the solid-state with two Cl^- anions and one water mol­ecule. Each component is involved in the hydrogen-bonding network, with one Cl^- anion and the O atom both being involved in three-centre associations, while the second Cl^- anion is involved in a four-centre association.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 15.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

no comment

S2. Experimental

The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.

S3. Refinement

All aromatic H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å. All H atoms involved in the hydrogen-bonding network were located on difference syntheses and both positional and thermal parameters refined.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. Molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids.

8-Hydrazinoquinoline dihydrochloride hydrate

Crystal data

C9H11N3·H2O·2Cl	Z = 2
Mr = 250.12	F(000) = 260
Triclinic, P1	Dx = 1.518 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9716 (14) Å	Cell parameters from 3835 reflections
b = 8.9866 (18) Å	θ = 2.9–27.5°
c = 9.986 (2) Å	µ = 0.57 mm^−1
α = 70.04 (3)°	T = 150 K
β = 89.20 (3)°	Plate, colourless
γ = 69.60 (3)°	0.40 × 0.30 × 0.10 mm
V = 547.2 (3) Å^3

Data collection

Bruker-Nonius KappaCCD area-detector diffractometer	2465 independent reflections
Radiation source: Bruker Nonius FR591 rotating-anode	2168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.804, Tmax = 0.945	l = −12→12
7519 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.1837P] where P = (Fo^2 + 2Fc^2)/3
2465 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1739 (2)	0.07021 (18)	0.21676 (16)	0.0155 (3)
H1	0.134 (3)	0.116 (3)	0.135 (3)	0.030 (6)*
C2	0.3176 (3)	−0.0843 (2)	0.25755 (19)	0.0191 (4)
H2	0.3641	−0.1364	0.1888	0.024*
C3	0.4012 (3)	−0.1711 (2)	0.40145 (19)	0.0211 (4)
H3	0.4996	−0.2840	0.4318	0.026*
C4	0.3395 (3)	−0.0915 (2)	0.49820 (18)	0.0188 (4)
H4	0.3994	−0.1481	0.5955	0.023*
C5	0.1176 (3)	0.1629 (2)	0.54967 (17)	0.0185 (4)
H5	0.1748	0.1122	0.6476	0.023*
C6	−0.0323 (3)	0.3219 (2)	0.50005 (18)	0.0185 (4)
H6	−0.0776	0.3813	0.5640	0.023*
C7	−0.1209 (3)	0.3991 (2)	0.35551 (18)	0.0170 (3)
H7	−0.2248	0.5097	0.3237	0.021*
C8	−0.0597 (2)	0.31715 (19)	0.26010 (16)	0.0129 (3)
N81	−0.1340 (2)	0.38149 (17)	0.11329 (14)	0.0154 (3)
H81	−0.188 (3)	0.313 (3)	0.091 (2)	0.024 (5)*
N82	−0.2880 (2)	0.54946 (17)	0.06257 (16)	0.0153 (3)
H82	−0.405 (4)	0.551 (3)	0.105 (2)	0.026 (5)*
H83	−0.233 (3)	0.620 (3)	0.070 (2)	0.017 (5)*
H84	−0.319 (4)	0.578 (3)	−0.031 (3)	0.034 (6)*
C9	0.1006 (2)	0.15379 (19)	0.30938 (16)	0.0135 (3)
C10	0.1875 (2)	0.0741 (2)	0.45477 (17)	0.0155 (3)
Cl1	0.65290 (6)	0.12401 (5)	0.09802 (4)	0.01981 (15)
Cl2	0.33779 (6)	0.50675 (5)	0.23075 (4)	0.01915 (14)
O1W	0.1078 (2)	0.22369 (16)	0.91537 (13)	0.0191 (3)
H1W	0.159 (4)	0.134 (4)	0.896 (3)	0.051 (8)*
H2W	0.001 (4)	0.266 (3)	0.875 (3)	0.033 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0183 (7)	0.0164 (7)	0.0118 (7)	−0.0062 (6)	−0.0005 (5)	−0.0049 (6)
C2	0.0201 (9)	0.0168 (8)	0.0209 (9)	−0.0056 (7)	0.0025 (7)	−0.0084 (7)
C3	0.0182 (8)	0.0153 (8)	0.0237 (9)	−0.0037 (7)	−0.0016 (7)	−0.0022 (7)
C4	0.0185 (8)	0.0199 (8)	0.0157 (8)	−0.0097 (7)	−0.0028 (6)	−0.0008 (7)
C5	0.0234 (9)	0.0257 (9)	0.0102 (7)	−0.0143 (7)	−0.0004 (6)	−0.0055 (7)
C6	0.0247 (9)	0.0242 (9)	0.0139 (8)	−0.0139 (7)	0.0046 (6)	−0.0109 (7)
C7	0.0193 (8)	0.0168 (8)	0.0169 (8)	−0.0070 (7)	0.0013 (6)	−0.0081 (7)
C8	0.0164 (8)	0.0136 (7)	0.0102 (7)	−0.0078 (6)	0.0000 (6)	−0.0038 (6)
N81	0.0203 (7)	0.0120 (6)	0.0112 (7)	−0.0016 (5)	−0.0034 (5)	−0.0053 (5)
N82	0.0178 (8)	0.0126 (7)	0.0131 (7)	−0.0026 (6)	−0.0018 (6)	−0.0044 (6)
C9	0.0160 (8)	0.0151 (8)	0.0116 (7)	−0.0080 (6)	0.0011 (6)	−0.0052 (6)
C10	0.0180 (8)	0.0184 (8)	0.0122 (7)	−0.0111 (6)	−0.0013 (6)	−0.0031 (6)
Cl1	0.0258 (3)	0.0132 (2)	0.0176 (2)	−0.00356 (17)	−0.00399 (16)	−0.00546 (17)
Cl2	0.0202 (2)	0.0218 (2)	0.0137 (2)	−0.00540 (17)	0.00096 (16)	−0.00665 (17)
O1W	0.0211 (7)	0.0165 (6)	0.0183 (6)	−0.0021 (5)	−0.0021 (5)	−0.0091 (5)

Geometric parameters (Å, º)

N1—C2	1.325 (2)	C6—H6	0.95
N1—C9	1.369 (2)	C7—C8	1.371 (2)
N1—H1	0.78 (2)	C7—H7	0.95
C2—C3	1.398 (3)	C8—N81	1.409 (2)
C2—H2	0.95	C8—C9	1.423 (2)
C3—C4	1.370 (3)	N81—N82	1.432 (2)
C3—H3	0.95	N81—H81	0.91 (2)
C4—C10	1.414 (2)	N82—H82	0.91 (2)
C4—H4	0.95	N82—H83	0.87 (2)
C5—C6	1.367 (3)	N82—H84	0.89 (3)
C5—C10	1.416 (2)	C9—C10	1.414 (2)
C5—H5	0.95	O1W—H1W	0.84 (3)
C6—C7	1.410 (2)	O1W—H2W	0.76 (3)
C2—N1—C9	123.19 (15)	C6—C7—H7	119.4
C2—N1—H1	117.0 (16)	C7—C8—N81	126.43 (15)
C9—N1—H1	119.7 (16)	C7—C8—C9	118.32 (14)
N1—C2—C3	120.21 (16)	N81—C8—C9	115.20 (14)
N1—C2—H2	119.9	C8—N81—N82	115.00 (13)
C3—C2—H2	119.9	C8—N81—H81	111.7 (13)
C4—C3—C2	119.24 (16)	N82—N81—H81	106.8 (13)
C4—C3—H3	120.4	N81—N82—H82	111.0 (13)
C2—C3—H3	120.4	N81—N82—H83	108.6 (13)
C3—C4—C10	120.66 (15)	H82—N82—H83	116.2 (19)
C3—C4—H4	119.7	N81—N82—H84	107.1 (15)
C10—C4—H4	119.7	H82—N82—H84	108 (2)
C6—C5—C10	119.82 (15)	H83—N82—H84	106 (2)
C6—C5—H5	120.1	N1—C9—C10	118.57 (15)
C10—C5—H5	120.1	N1—C9—C8	120.56 (14)
C5—C6—C7	121.10 (15)	C10—C9—C8	120.87 (15)
C5—C6—H6	119.4	C4—C10—C9	118.04 (15)
C7—C6—H6	119.4	C4—C10—C5	123.25 (15)
C8—C7—C6	121.11 (16)	C9—C10—C5	118.71 (15)
C8—C7—H7	119.4	H1W—O1W—H2W	104 (2)
C9—N1—C2—C3	0.6 (2)	N81—C8—C9—N1	0.5 (2)
N1—C2—C3—C4	−2.9 (3)	C7—C8—C9—C10	3.2 (2)
C2—C3—C4—C10	2.3 (2)	N81—C8—C9—C10	−179.41 (13)
C10—C5—C6—C7	0.6 (2)	C3—C4—C10—C9	0.5 (2)
C5—C6—C7—C8	0.1 (2)	C3—C4—C10—C5	−179.92 (16)
C6—C7—C8—N81	−179.04 (15)	N1—C9—C10—C4	−2.8 (2)
C6—C7—C8—C9	−1.9 (2)	C8—C9—C10—C4	177.10 (14)
C7—C8—N81—N82	0.2 (2)	N1—C9—C10—C5	177.62 (14)
C9—C8—N81—N82	−177.01 (13)	C8—C9—C10—C5	−2.5 (2)
C2—N1—C9—C10	2.3 (2)	C6—C5—C10—C4	−178.98 (15)
C2—N1—C9—C8	−177.57 (14)	C6—C5—C10—C9	0.6 (2)
C7—C8—C9—N1	−176.98 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W^i	0.78 (2)	2.05 (2)	2.817 (2)	165 (2)
N81—H81···Cl1^ii	0.91 (2)	2.32 (2)	3.1983 (16)	164.5 (18)
N82—H82···Cl2^ii	0.91 (2)	2.25 (2)	3.1476 (18)	169.8 (18)
N82—H83···O1W^iii	0.87 (2)	1.94 (2)	2.808 (2)	178.7 (19)
N82—H84···Cl2^iv	0.89 (3)	2.39 (3)	3.1805 (17)	149.1 (19)
O1W—H1W···Cl1^v	0.84 (3)	2.21 (3)	3.0348 (17)	164 (2)
O1W—H2W···Cl2^iii	0.76 (3)	2.47 (3)	3.180 (2)	158 (2)

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, −y, −z+1.